It’s a sad Thursday in Boston, as beloved former mayor Tom Menino died at age 71.

Menino, the city’s longest-serving mayor at 21 years, lost his battle with cancer at approximately 9 a.m., while accompanied by family and friends. Even after being diagnosed with the disease, Menino remained high-spirited as always.

Menino loved everything about Boston, including its sports. While he’ll always be remembered as an outstanding mayor first and foremost, he also left a smile on many faces with his humorous, unforgettable, sports-related gaffes.